12 Of The Most Entertaining Rom Coms From The 2000s

The 2000s was the decade of the romantic comedy.

There was nothing better than watching Kate Hudson, Reese Witherspoon and Jennifer Aniston fall for young Hugh Grant and Mathew McConaugheyForget Cinderella and Prince Charming, these were the real fairytales.

There’s been a distinct fall of graces in the rom-com genre over recent years. Yes, there have been plenty of beautiful love stories, like The Age of Adaline, The Best of Me, and The Fault in Our Stars, but where is the comedic relief? Minus Trainwreck (Amy Schumer’s #1 fan over here), there has been a distinct lack of laughs in these love stories. And let’s be honest: dating is often a bit more comedy, a bit less romance.

Below is the essential list of romantic comedies that will have you laughing, crying and swooning, all at once.

1. How to Lose a Guy in 10 Days (2003)

Andie Anderson was the original man repeller (sorry Leandra). Kate Hudson plays Andie, a magazine advice columnist, who sets out to see what it takes to get a man to leave you in only 10 days—all in the name of research! Apparently, it’s incredibly hard, even when you name his genitals, make him eat vegan food, and interrupt his sports games.

2. Bridget Jones’s Diary (2001)

Bridget Jones’ Diary has been a cultural zeitgeist since it first came out in 2001. Renee Zellweger plays the insecure Bridget Jones’ and we see Bridget go through all the embarrassments of life, from horrific speeches to misreading party invitations. Most importantly, we see Bridget struggle with her weight, smoking, drinking, men, and everything in between.

3. The Wedding Planner (2001)

Is there anything better than early 2000s J. Lo? The Wedding Planner is one of J. Lo’s finest moments as she plays a, duh, wedding planner who is rescued from a collision with a dumpster by a handsome pediatrician played by a very tan Mathew McConaughey.

4. 13 Going on 30 (2004)

The film follows Jenna Rink, an embarrassed, awkward, prepubescent 13 year old whose wishes to become older come true. Luckily when she wakes up age 30 she not only looks like Jennifer Garner but has a killer closet, a magazine editor position and a cute-love interest in the form of Mark Ruffalo.

5. The Break Up (2006)

It’s hard to pick a fave Jennifer Aniston rom-com as there was a period of time where she seemed to pump them out nonstop. The Break Up is great though, because it is so damn relatable. We all know the price of living is crazy in pretty much EVERY American city, so when Brooke (Aniston) and Gary (Vince Vaughn) break up and then both refuse to move out of their shared condo, I’m like yup, I feel you both.

6. Legally Blonde (2001)

The 2001 hit Legally Blonde articulates some of the best and smartest subverting of blonde stereotypes to ever hit the screen. Elle Woods’ niche knowledge of fashion, femininity and pop culture, combined with her tenacious hard work helps her to eventually become one of the top law students in her class at Harvard Law.

7. Juno (2007)

It’s the only romantic comedy in this list to win an Academy Award and earn three other Oscar noms, and with good reason. The awkwardness of Ellen Page and Michael Cera’s high school affair is both endearing and hilarious. The film takes an intense topic, whether or not Page’s character Juno should keep, abort, or give up her baby for adoption, and still manages to have multiple laugh out loud moments.

8. Knocked Up (2007)

Katherine Heigl, another staple of the romantic comedy genre, shines alongside Seth Rogen in this quintessential Judd Apatow comedy about the consequences of an unexpected pregnancy. There is nudity, expletives, and lots of inappropriate humor. It’s everything we love and crave in an Apatow film.

9. 50 First Dates (2004)

Okay, the premise might sound a little, um, nonconsensual, but somehow Adam Sandler and Drew Barrymore manage to make this an enviable love story for the ages. Basically Barrymore’s character, Lucy, has short term memory loss so every day is a new day for her. Luckily Henry (Sandler) decides not to take advantage of her (yay for nice men!) and sets out to woo her everyday.

10. 500 Days of Summer (2009)

Zooey Deschanel plays the ultimate manic pixie dream girl, Summer, who expectantly dumps her boyfriend after 500 days together. Unlike most other rom-coms, the love is over before the film even begins, but it’s still equally cutesy as Tom (Joseph Gordon-Levitt) flashbacks to their memories together to find where the relationship went wrong.

11. Nick and Norah’s Infinite Playlist (2008)

This was the movie for hipsters everywhere when it came out in 2008 and it doesn’t disappoint now. Michael Cera and Kat Dennings are freaking adorable as Nick and Norah. They spend the night running around New York City to find a secret show of their favorite band, Where’s Fluffy? It’s the ultimate young-love-in-the-city film.

12. Love Actually (2003)

While it may be most appropriate to watch during the holidays, who says you can’t fill your room with some Christmas cheer, and some Hugh Grant (yes, please). The film also features a young Andrew Lincoln in his pre-zombie apocalypse days, a baby faced Kiera Knightley, an adorable Thomas Brodie-Sangster, and that’s really only a taster of the Brits in this film.

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